Showing Compound Card for beta-Hydroxybutyric acid (CDB006332)

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Record Information
Version1.0
Created at2020-09-11 15:49:24 UTC
Updated at2022-12-13 23:36:27 UTC
CannabisDB IDCDB006332
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common Namebeta-Hydroxybutyric acid
Description3-Hydroxybutyric acid, also known as 3-hydroxybutyrate or 3-hydroxybuttersaeure, belongs to the class of organic compounds known as beta hydroxy acids and derivatives. Beta hydroxy acids and derivatives are compounds containing a carboxylic acid substituted with a hydroxyl group on the C3 carbon atom. A straight-chain 3-hydroxy monocarboxylic acid comprising a butyric acid core with a single hydroxy substituent in the 3- position; a ketone body whose levels are raised during ketosis, used as an energy source by the brain during fasting in humans. 3-Hydroxybutyric acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 3-Hydroxybutyric acid exists in all living species, ranging from bacteria to humans. Outside of the human body, 3-Hydroxybutyric acid is found, on average, in the highest concentration within milk (cow). This could make 3-hydroxybutyric acid a potential biomarker for the consumption of these foods. 3-Hydroxybutyric acid is a potentially toxic compound. 3-Hydroxybutyric acid, with regard to humans, has been found to be associated with several diseases such as alzheimer's disease, colorectal cancer, 3-hydroxydicarboxylic aciduria, and crohn's disease; 3-hydroxybutyric acid has also been linked to the inborn metabolic disorder 2-ketoglutarate dehydrogenase complex deficiency.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
(1)-3-Hydroxybutyric acidChEBI
3 HBAChEBI
3-HydroxybuttersaeureChEBI
3-OH-Butyric acidChEBI
beta-Hydroxy-N-butyric acidChEBI
beta-Hydroxybutanoic acidChEBI
beta-HydroxybuttersaeureChEBI
beta-Hydroxybutyric acidChEBI
BHBAChEBI
DL-beta-Hydroxybutyric acidChEBI
(1)-3-HydroxybutyrateGenerator
3-OH-ButyrateGenerator
b-Hydroxy-N-butyrateGenerator
b-Hydroxy-N-butyric acidGenerator
beta-Hydroxy-N-butyrateGenerator
Β-hydroxy-N-butyrateGenerator
Β-hydroxy-N-butyric acidGenerator
b-HydroxybutanoateGenerator
b-Hydroxybutanoic acidGenerator
beta-HydroxybutanoateGenerator
Β-hydroxybutanoateGenerator
Β-hydroxybutanoic acidGenerator
b-HydroxybuttersaeureGenerator
Β-hydroxybuttersaeureGenerator
b-HydroxybutyrateGenerator
b-Hydroxybutyric acidGenerator
beta-HydroxybutyrateGenerator
Β-hydroxybutyrateGenerator
Β-hydroxybutyric acidGenerator
DL-b-HydroxybutyrateGenerator
DL-b-Hydroxybutyric acidGenerator
DL-beta-HydroxybutyrateGenerator
DL-Β-hydroxybutyrateGenerator
DL-Β-hydroxybutyric acidGenerator
3-HydroxybutyrateGenerator
3-Hydroxy-butanoateHMDB
3-Hydroxy-butanoic acidHMDB
3-Hydroxy-butyrateHMDB
3-Hydroxy-butyric acidHMDB
3-HydroxybutanoateHMDB
3-Hydroxybutanoic acidHMDB
BiopolHMDB
DL-3-HydroxybutyrateHMDB
DL-3-Hydroxybutyric acidHMDB
beta Hydroxybutyric acidHMDB
3 Hydroxybutyric acidHMDB
beta HydroxybutyrateHMDB
(+ -)-3-Hydroxybutyric acidHMDB
3 HydroxybutyrateHMDB
Chemical FormulaC4H8O3
Average Molecular Weight104.1045
Monoisotopic Molecular Weight104.047344122
IUPAC Name3-hydroxybutanoic acid
Traditional Name3 hydroxybutyrate
CAS Registry NumberNot Available
SMILES
CC(O)CC(O)=O
InChI Identifier
InChI=1S/C4H8O3/c1-3(5)2-4(6)7/h3,5H,2H2,1H3,(H,6,7)
InChI KeyWHBMMWSBFZVSSR-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as beta hydroxy acids and derivatives. Beta hydroxy acids and derivatives are compounds containing a carboxylic acid substituted with a hydroxyl group on the C3 carbon atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassHydroxy acids and derivatives
Sub ClassBeta hydroxy acids and derivatives
Direct ParentBeta hydroxy acids and derivatives
Alternative Parents
Substituents
  • Short-chain hydroxy acid
  • Beta-hydroxy acid
  • Fatty acid
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Not Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-0.5ALOGPS
logP-0.39ChemAxon
logS0.71ALOGPS
pKa (Strongest Acidic)4.41ChemAxon
pKa (Strongest Basic)-2.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity23.46 m³·mol⁻¹ChemAxon
Polarizability10.01 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-0007-9000000000-7fc414806153ebd8822c2014-09-20View Spectrum
GC-MSbeta-Hydroxybutyric acid, non-derivatized, GC-MS Spectrumsplash10-0002-0900000000-92be5c49a099fe1d9865Spectrum
GC-MSbeta-Hydroxybutyric acid, non-derivatized, GC-MS Spectrumsplash10-01ot-1920000000-c93138bf9d35643fef30Spectrum
GC-MSbeta-Hydroxybutyric acid, 2 TMS, GC-MS Spectrumsplash10-00dj-8900000000-e632e14fb4be28bdb786Spectrum
GC-MSbeta-Hydroxybutyric acid, 2 TMS, GC-MS Spectrumsplash10-014l-1900000000-e192caba63f034040624Spectrum
GC-MSbeta-Hydroxybutyric acid, non-derivatized, GC-MS Spectrumsplash10-0002-0900000000-92be5c49a099fe1d9865Spectrum
GC-MSbeta-Hydroxybutyric acid, non-derivatized, GC-MS Spectrumsplash10-01ot-1920000000-c93138bf9d35643fef30Spectrum
GC-MSbeta-Hydroxybutyric acid, non-derivatized, GC-MS Spectrumsplash10-00dj-8900000000-e632e14fb4be28bdb786Spectrum
GC-MSbeta-Hydroxybutyric acid, non-derivatized, GC-MS Spectrumsplash10-014l-1900000000-e192caba63f034040624Spectrum
GC-MSbeta-Hydroxybutyric acid, non-derivatized, GC-MS Spectrumsplash10-0002-0900000000-d06c5ac1a3733a38ea05Spectrum
Predicted GC-MSbeta-Hydroxybutyric acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0007-9000000000-63f261a4dc876e264246Spectrum
Predicted GC-MSbeta-Hydroxybutyric acid, 2 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-01ei-9710000000-2652bd46b41e50defdb0Spectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-0a4i-9200000000-4156904e7472b5e972492012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-0a4i-9300000000-505ae46abb0c49c78b1e2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-0zfr-9600000000-dfed69c37c1a4d7944402012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-0zfr-4900000000-537084557f5986f16b312012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0zfr-4900000000-537084557f5986f16b312017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-IT , positivesplash10-000i-9000000000-7f0ec480b3c3c3911acd2017-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kr-9100000000-05c4623b015ff4300a6d2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05n0-9000000000-cbe0653845ffe4dc6ad42016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-e55d47308c7464e4cb222016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0zfr-8900000000-06dfbf939f6d19983ebe2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0pb9-9200000000-48b6e9b8656d41bff9cf2016-09-12View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9000000000-f7d61596ff4428fe6b092016-09-12View Spectrum
NMR
TypeDescriptionView
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, D2O, experimental)Spectrum
2D NMR[1H, 1H]-TOCSY 2D NMR Spectrum (experimental)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Cannabis CultivarStatusValueReferenceDetails
Alien DawgDetected and Quantified0.00515 mg/g dry wt
    • David S. Wishart,...
 details
GabriolaDetected and Quantified0.00684 mg/g dry wt
    • David S. Wishart,...
 details
Island HoneyDetected and Quantified0.00468 mg/g dry wt
    • David S. Wishart,...
 details
QuadraDetected and Quantified0.00924 mg/g dry wt
    • David S. Wishart,...
 details
Sensi StarDetected and Quantified0.00821 mg/g dry wt
    • David S. Wishart,...
 details
Tangerine DreamDetected and Quantified0.00897 mg/g dry wt
    • David S. Wishart,...
 details
HMDB IDHMDB0000357
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB021797
KNApSAcK IDNot Available
Chemspider ID428
KEGG Compound IDC01089
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia Link3-hydroxybutyrate
METLIN ID125
PubChem Compound441
PDB IDNot Available
ChEBI ID20067
References
General ReferencesNot Available